A friend is running CC with all updates installed on an I-Mac. He selects a raw photo in Lightroom and opens it in Photoshop. He then edits the photo using a Photoshop plugin such as Topaz Simplify. When he chooses File > Save from the menu sometimes the file is saved in the folder with the raw file and the newly created .psd file is entered in the Lightroom catalog as it should be. Other times the file save dialog appears prompting him for a name and location to save the newly created .psd. Even if he accepts the default name and location the new .psd file is not entered into the Lightroom catalog. He must synchronize the folder to get the photo into the LR catalog. It is as though Photoshop sometimes forgets that the photo was opened from LR. This guy is not dreaming. I have watched this happen on his Mac. I am running CC on Win 10 Pro and have never seen this happen. What is causing this behavior and how can we fix the problem? Thanks.

This issue usually occurs when you click on save as instead of save and Photoshop asks for the name and location to save the file. If you sure that Photoshop doing the same thing when you click on save then you may try resetting the Photoshop preferences and check if that helps.